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3rd January 2012 @ 03:40
Product obtained.

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Scale-up of PMY 12-4.

Coupling of acid PMY 8-3 and 4-aminoantipyrine for a analogue of TCMDC-123794 that does not contain the ester linker. Using T3P as coupling reagent.

Reaction Scheme

Reaction start time: 16.36 03/01/12
PMY 8-3 (150 mg, 0.63 mmol, 1 equiv.), 4-aminoantipyrine (144 mg, 0.72 mmol, 1.1 equiv.) were dissolved in EtOAc (approx. 3 mL) and pyridine (0.3 mL, 3.9 mmol, 6 equiv.) and placed in a room temperature water bath. T3P 50% in EtOAc (0.78 mL, 0.129 mmol, 2 equiv.) was added. Stirred overnight. TLC shows new product. 0.5 M HCl (20 mL) added and the mixture extracted with EtOAC (3 × 10 mL). The combined organic extracts were washed with water (2 × 10 mL) and brine then dried (MgSO4) and concentrated to a brown solid (170 mg). Purification by chromatography (3% MeOH/DCM) gave recovered starting material (101 mg) and product (30 mg).

TLC (10% MeOH/DCM) visualised with UV and vanillin:
TLC


NMR:
1H NMR product
1H NMR recov SM


Risk and Hazard Assessment:
See Synthesis of TCMDC-123794 Side-chain (PMY 5-1) and Synthesis of TCMDC-123812 using T3P (PMY 10-4)

See also:
Coupling of acid PMY 8-2 and 4-aminoantipyrine using T3P for a linker-less analogue of TCMDC-123794 (PMY 12-4)
Coupling of acid PMY 8-2 and 4-aminoantipyrine using EDC for a linker-less analogue of TCMDC-123794 (PMY 12-3)
Coupling of acid PMY 8-2 and 4-aminoantipyrine for a linker-less analogue of TCMDC-123794 (PMY 12-2)
Coupling of acid PMY 8-2 and 4-aminoantipyrine for a linker-less analogue of TCMDC-123794 (PMY 12-1)
Linked Entries
Attached Files
Scheme
TLC
1H NMR recov SM
1H NMR product